HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$164+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jun 22 — Jun 291
Sun 6/22
Sun 6/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated June 17, 2025.

Round-trip from

$225
(United Airlines)

One-way from

$164
(Delta)

Popular in

December

Cheapest in

November

Average price

$515
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 17, 2025.

This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2710:51 amMSN - SJU
2 stops12h 06mUnited Airlines
Tue 9/301:05 amSJU - MSN
2 stops11h 40mUnited Airlines
Deal found 6/16$225
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:48 amMSN - SJU
1 stop7h 04mAmerican Airlines
Tue 10/76:30 amSJU - MSN
2 stops9h 38mAmerican Airlines
Deal found 6/16$310
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:45 amMSN - PUJ
1 stop6h 32mDelta
Tue 11/43:42 pmPUJ - MSN
1 stop8h 52mDelta
Deal found 6/15$363
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:48 amMSN - PUJ
1 stop6h 37mAmerican Airlines
Wed 9/103:25 pmPUJ - MSN
1 stop8h 45mAmerican Airlines
Deal found 6/17$376
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:30 amMSN - PUJ
1 stop7h 32mUnited Airlines
Wed 12/172:55 pmPUJ - MSN
1 stop7h 50mUnited Airlines
Deal found 6/15$419
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:16 amMSN - NAS
1 stop5h 09mAmerican Airlines
Tue 7/226:30 pmNAS - MSN
1 stop17h 16mAmerican Airlines
Deal found 6/15$469
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:48 amMSN - MBJ
1 stop7h 06mAmerican Airlines
Sat 10/41:05 pmMBJ - MSN
1 stop10h 21mAmerican Airlines
Deal found 6/16$488
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/306:40 amMSN - MBJ
2 stops8h 30mUnited Airlines
Wed 8/64:12 pmMBJ - MSN
2 stops21h 42mUnited Airlines
Deal found 6/15$495
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:00 amMSN - SDQ
2 stops9h 52mDelta
Wed 11/54:15 pmSDQ - MSN
1 stop8h 19mDelta
Deal found 6/15$519
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2410:50 amMSN - SJU
1 stop10h 58mDelta
Sat 7/54:18 pmSJU - MSN
1 stop8h 10mDelta
Deal found 6/16$527
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:45 amMSN - GCM
1 stop6h 30mAmerican Airlines
Sat 8/302:15 pmGCM - MSN
1 stop9h 12mAmerican Airlines
Deal found 6/16$548
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:45 amMSN - NAS
1 stop5h 09mDelta
Tue 10/71:23 pmNAS - MSN
1 stop10h 11mDelta
Deal found 6/15$549

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 17, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/27

10:51 am-11:57 pm

2 stops12h 06m

San Juan Luis Munoz Marin Intl

Tue 9/30

1:05 am-11:45 am

2 stops11h 40m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

7:48 am-3:52 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

Tue 10/7

6:30 am-3:08 pm

2 stops9h 38m

$310

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Fri 9/5

7:48 am-3:25 pm

1 stop6h 37m

Punta Cana

Wed 9/10

3:25 pm-11:10 pm

1 stop8h 45m

$376

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 7/15

7:16 am-1:25 pm

1 stop5h 09m

Nassau Intl

Tue 7/22

6:30 pm-10:46 am

1 stop17h 16m

$469

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 7/30

6:40 am-3:10 pm

2 stops8h 30m

Montego Bay Sangster Intl

Wed 8/6

4:12 pm-1:54 pm

2 stops21h 42m

$495

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 7/30

2:35 pm-3:35 pm

2 stops24h 00m

Punta Cana

Wed 8/6

4:35 pm-3:03 pm

2 stops23h 28m

$510

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 6/24

6:45 am-2:30 pm

1 stop7h 45m

Montego Bay Sangster Intl

Sat 6/28

5:05 pm-10:52 am

1 stop17h 47m

$513

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Wed 10/22

7:00 am-5:52 pm

2 stops9h 52m

Santo Domingo Las Americas

Wed 11/5

4:15 pm-10:34 pm

1 stop8h 19m

$519

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 8/23

6:45 am-1:15 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sat 8/30

2:15 pm-11:27 pm

1 stop9h 12m

$548

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Fri 10/3

5:45 am-11:54 am

1 stop5h 09m

Nassau Intl

Tue 10/7

1:23 pm-10:34 pm

1 stop10h 11m

$549

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 24 results
1
2
3

Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated June 17, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Madison to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,965 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,965 reviews
Delta
8.0
Very good
7,965 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,809 reviews
Delta
8.0
Very good
7,965 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,965 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Oranjestad Reina Beatrix or Madison Truax Field - Punta Cana, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Seattle flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Newark flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Boston flights
O'Hare Intl to Denver flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Minneapolis to Seattle flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to San Francisco flights
Minneapolis to LaGuardia flights
Minneapolis to Las Vegas flights
Minneapolis to Denver flights
O'Hare Intl to San Diego flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Portland flights
O'Hare Intl to Philadelphia flights
Minneapolis to Newark flights
O'Hare Intl to Hobby flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Ontario flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Vancouver Intl flights
Minneapolis to Orlando flights
Minneapolis to Sky Harbor Intl flights
Milwaukee to Seattle flights
Minneapolis to Dallas/Fort Worth flights
Minneapolis to Cancún flights
Milwaukee to Denver flights
O'Hare Intl to Tampa flights
O'Hare Intl to Burbank flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Salt Lake City flights
Milwaukee to LaGuardia flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Nashville flights

Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$698FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$330Average$641FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$650FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.